3,4-dihydro-2H-pyran → 9-Tetrahydropyranyloxy-1-bromononane

HRID 1799651Notes

Reaction equation

HRID 1799651 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][O:12]1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 1087001-Nonanol, 9-bromo-HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 109467299-Tetrahydropyranyloxy-1-bromononaneYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 9-bromo-1-nonanol (2.00 g, 8.96 mmol), 3,4-dihydro-2H-pyran (792 mg, 9.41 mmol), and pyridinium toluene-4-sulfonate (1.08 g, 4.30 mmol) in dichloromethane (34 mL) was stirred at room temperature for 16 h, then washed with 2 M aq. sodium carbonate solution and brine, dried over sodium sulfate, filtered, and evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient) produced 2-(9-bromo-nonyloxy)-tetrahydro-pyran (2.45 g, 89%). Colorless oil, m/e=324.1 ([M+NH4]).

Workup

  1. washwashed with 2 M aq. sodium carbonate solution and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-a5f071b285554283a3f763467afaf991
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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